Building a career in venture
I recently delivered a quick 15-minute presentation on building a career in venture for the Liminal online conference .
It’s a question I get asked about a lot, especially by younger women, which I am thrilled about. One of the most positive and exciting developments in startups today is the greater diversity of backgrounds of investors. Not just identity, but the types of careers and life experiences people bring to this job.
I have synthesised some advice for those who aspire to enter venture and maybe don’t come from central casting. You can re-watch the full presentation including the excellent Q&A here.
If you need the slightly shorter, written version, see below.
About Me
I studied a BA/LLB majoring in history at UNSW. Like most people who do a BA/LLB, I had no burning passion to become a lawyer, but I did it anyway. In my fourth year of uni I applied for summer clerkships and was accepted at Minter Ellison, a big global law firm in Sydney. 4 years later I was a corporate M&A and transaction disputes lawyer.
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In 2010, just as the world was recovering from the (last) global financial crisis, I decided I needed to scratch my entrepreneurial itch before the golden handcuffs were fastened for good. I took a 1 year leave of absence and eventually through a lot of hustle and luck, found my way into a marketing then product role at a fast-growing startup, SurfStitch.com as employee #20ish.
After 3 years at SurfStitch, I felt my learning plateau and left to start my own startup, CapacityHQ, which got into the Startmate accelerator. We ultimately pivoted and failed somewhat elegantly. I learned a lot about what is required to built a successful startup.
Between startups and out of runway, in 2015, I joined Blackbird as their first hire.
In 2018, I was promoted to Partner.
Late in 2019 I helped launch our inaugural New Zealand fund, and in January 2020 moved to Auckland, New Zealand to head up our office here.
In August 2020, Blackbird raised its fourth fund, a AU$500M fund and I became an equal partner with Niki, Rick and Nick.
Oh, and in July 2019 I had my first baby, which has been the biggest thrill of all.
It’s been quite a ride. 🎢
From my experiences and observations over that time, I have 3 pieces of advice.
Optimise for learning, not money
It was 2010, in the middle of the last GFC, six months after buying my first apartment, I was 28, quit my lawyer job and moved home with my mum and started working 3 part-time jobs, 7 full days and 1 evening a week.
I gave myself one year to find a new career that would replace my previous lawyer’s salary. My first job at SurfStitch doing SEO was casual for 3 weeks and paid $25/hr.
A 3 week SEO gig at SurfStitch turned into an Email Marketing role which turned into a Product role which turned into launching the European headquarters and moving to France for 2 years.
I left SurfStitch after 3 years when my learning had plateau’d. I started a company because I wanted to learn more. I paid myself $25k/year as a founder.
When I first joined Blackbird, the money wasn’t that great. But it was a fortune compared to what I earned as a founder, and it was guaranteed to turn up in my account every month, which you don’t take for granted once you’ve been a founder!
I was never greedy about money. I was always greedy for learning and experience. I knew that if I surrounded myself with people that I could learn from, and made myself useful to them, the money would eventually follow.
I would never have gotten the Blackbird job without going through Startmate; I would never have started my own company if I hadn’t joined SurfStitch; I would never have joined SurfStitch if I hadn’t quit law and hustled working minimum wage to get startup experience.
It’s 2020, not 2010. It’s easier for smart, hustle-y people to get into startups these days. One of the best paths is to do the Startmate Fellowship. Applications close this week. What have you got to lose?
Say ‘Yes’ to things you’re not qualified to do
Research tells us that women are less likely to put themselves forward for roles they don’t believe they are fully qualified for.
The only job I’ve done that I was truly qualified to do was law — and it didn’t make me happy.
My first startup jobs were doing SEO, Social Media Marketing, then Email Marketing, then Product Management. I didn’t know anything about those things, but outside of Silicon Valley in 2010, almost nobody did. I could read, write and research, I had contributed to some early online media sites and built my own blog so I knew a tiny bit about how the web worked.
When I joined Blackbird, I knew nothing about managing a VC fund. I’d never studied accounting or finance. As a lawyer, I could read legislation and understood regulated environments. As a product manager and founder, I became good at analysing problems and coming up with solutions pretty self-sufficiently and teaching myself almost anything.
If you have the initiative to join a webinar or read this far into a blog, then you’re probably the sort of person who can afford to back themselves to learn.
You don’t need someone to give you permission.
Build a honeypot for dealflow
There isn’t really a corporate ladder for careers in VC. It is possible to join as an analyst and work your way up to Partner, but historically those cases have been rare.
The traditional way to get into VC is to be an ex-founder and senior operator at a successful startup. You start angel investing with your millions and eventually get tapped on the shoulder, or start your own fund.
However, if that’s not you, don’t worry, because that’s not the only way to get into VC.
The single most important thing as an investor is your ability to build a honeypot for dealflow.
You can do this without much, or any money to invest, if you really think about it.
Here are some strategies you can consider.
Influencer Marketing
Harry Stebbings is a British podcaster turned VC
He was 17 when he started the 20 Minute VC podcast in the attic of his mother’s house. It was a simple format, he’d interview VCs and angels for 20 minutes. When he started there weren’t that many startup podcasts, and only a couple focussed on venture investing. The field was wide open.
Harry had a bubbly engaging style. As a non-expert himself, he asked all the ‘dumb’ questions others were too afraid to ask. It was so useful to outsiders trying to learn what was inside the black box of VC.
It was pretty easy to get guests — it’s flattering to be invited on a podcast, and most investors love the sound of their own voice 😂 . At the end of every interview, Harry would ask for suggestions for other guests. Gradually the guests introduce you to folks further and further up the foodchain until one day, you’re interviewing Benchmark’s Peter Fenton.
The podcast became incredibly popular. He started interviewing founders for his podcast. Knowing that Harry knew investors, founders would ask him for advice and introductions. Bingo. Dealflow.
Through the podcast, he met his now co-founder, Fred Destin, formerly of Accel in London, and now they run Stride VC together. Harry also has a new US microfund. Harry is 24.
Build a shadow track record
Sydney Paige Thomas is a Senior Associate at Precursor Ventures which is a Silicon Valley pre-seed VC fund. They invest in companies right at the beginning, a couple of people, an idea, possibly some very bad early version of a product.
When Sydney started out trying to get into venture, she didn’t have money to invest in startups, but wanted to build a track record.
She published her thesis about internet companies that give agency to people and started a podcast ‘Be About It’ interviewing pre-seed stage founders.
Over two seasons, she build a ‘track record’ of interviewees.
She tracked which companies went on to raise Series A capital. This would be a proxy for whether she could identify potential winners at pre-seed stage and give someone the confidence to hire her in an investing role. Also, it shows great tenacity.
Now, if you do have some money to invest, can you convince founders to let you invest $1k, $2k, $5k?
It seems like a laughably small amount, but the point for you is to show that you can find and convince founders to let you into the round. I would argue it is more impressive that founders let you invest a tiny amount then if you invest a large amount. Less than $10k barely makes the admin worth it for the founder. The fact that they will do it just to have you in the round shows they want you, not just your money.
Ultimately, money is a commodity. When you are a VC and you are competing against other VCs, you need to have something more than money to offer.
My first angel cheques were laughably small — like $2k. But they taught me so much at the time — how to think about companies and assess founders, how to form a thesis, what your cognitive traps are — and they are still teaching me lessons today.
Whether you invest or not, if you build a shadow portfolio and maintain a good relationship with the founders, you will be able to track the value of the company. You can answer the question, ‘if I was investing out of a fund and was able to get 15–20% ownership, that would be worth X today. Give me a job!’.
Community Building
Bri’s strategy was to build a SaaS community. As the organiser of the community, she put herself in the slipstream of exactly the kind of dealflow that she would like to invest in.
She is the creator of SaaS School. Operators from Airtable, Dropbox, Drift, Slack, Twilio deliver talks and office hours with founders of SaaS companies with more than $1M ARR. This put her in the centre of a community of SaaS experts who attract founders who want to learn from them. Early stage founders applied to be part of SaaS school giving her unfair access to dealflow.
Brianne is an incessant blogger and has relentless energy and hustle.
Her first fund was a US$5M backed by Marc Andreessen, Alexis Ohanian, Zoom CEO Eric Yuan.
The community-building model can be executed so many different ways. You can build communities around stage (eg pre-seed, pre-company), business models (eg enterprise, product-led growth, marketplaces, open source), sector (eg software, hardware, life sciences, fintech ), founder identity, geography, the list goes on.
Just Be Extraordinarily Helpful
This one is quite simple. Just be the person who works the hardest for the founders, who does the work no-one else has the time or energy to do.
Many Aussie startup people will know Rayn Ong either personally or through Twitter. This is a photo of him with the Propeller co-founders, Rory San Miguel and Francis Vierboom. Rayn was the chief wrangler/helper for the Seed round of Propeller in 2015 (and many other companies besides). Propeller recently raised $26M, is worth over $100M and is one of the rising stars of the Blackbird and Startmate portfolio.
I would say that Rayn made his reputation on the Propeller Seed deal. He helped round up the other angels and get them into line, helped coordinate the term sheets, cap tables, deal documents and due diligence. Basically, he did as much as he could to make the experience fast and frictionless for the founders. He will also take your t-shirt and wear it everywhere. Free advertising!
The point is: every founder is doing at least 3 or 4 jobs — they will happily give at least 1 job away to someone genuinely useful.
What can you do to be helpful?
You must have some skills that you’ve acquired from somewhere that equip you to help.
A common mistake here is thinking your day job is what you can be most helpful with. If you’re a property lawyer, please do not start helping startups negotiate their seed round investment docs! You need to work out what is the Venn diagram of things you are genuinely useful for and what startups need. Don’t over-assume your expertise. Invite feedback. But no-one will resent you for offering to help.
One Final Thought
In the Liminal webinar Q&A, someone asked me how to deal with imposter syndrome. I don’t think anyone, much less myself, has this truly worked out.
However, I shared this quote from Barack Obama from the Humans of New York blog on when he felt the most broken. It made a huge impact on me when I first read it. I printed it out and it sits on my desk every day. One webinar attendee coincidentally also had it printed out on her desk.
So in case it helps you too, I wanted to share it. A little Obama every day goes a long way!
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